I think the implication was that he may have had some hand (or other body part) in the creation of that situation. It wasn't just some criminals saying "oh, a trucker, this will be easy money".

Not sure that distinction matters? In the “guns prevent violence” framing, the pander should have been afraid of the alleged john being armed, and not attempted physical violence.

You could be right, but it could also be that it was common knowledge that he was anti-gun because he never was shy of sharing his opinion, and it's very common for the same truckers to do the same routes repeatedly. I don't think there's enough evidence either way in this anecdote to make any reasonable conclusions.

If you think criminals don't consider the risk of being shot when picking their targets, I'm afraid it is you who is fantasizing. Robberies aren't "crimes of passion" where emotions overrule normal common sense.

Yet the guy was still assaulted, despite truckers being a prime demographic for packing heat.

I don’t think you have any sources to back that up.